A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Oct 19 - Oct 20
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Oct 20 - Oct 21
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Oct 23 - Oct 25
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Oct 30 - Nov 1

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Our top choices for Hillsdale hotels

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.
A snow-covered landscape with a house and a sign that reads "the brooks".
A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.
A compact kitchen with a wooden countertop, a coffee machine, and a small shelf with a hair dryer and cups.

1. The Brooks Motel

The Brooks Motel
Hillsdale
United States
Nelson
₩194,534
₩217,880 total
includes taxes & fees
Oct 21 - Oct 22
The Brooks Motel
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A house with a stone patio and wooden stools.

2. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Stacy
₩202,452
₩226,746 total
includes taxes & fees
Nov 19 - Nov 20
Little Cat Lodge
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.
A wooden wall with a white pendant light fixture.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

3. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
₩377,353
₩466,107 total
includes taxes & fees
Nov 11 - Nov 12
Prospect Berkshires
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.
A hotel room with a bathroom, a bed, a desk, and a nightstand.
A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.
A Quality Inn sign, a brick building, and a parking lot with cars.

4. Quality Inn Great Barrington

Quality Inn Great Barrington
Downtown Great Barrington
United States
Scott Patterson
₩100,694
₩112,475 total
includes taxes & fees
Nov 9 - Nov 10
Quality Inn Great Barrington
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
United States
Md
₩191,665
₩214,090 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.
A modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.
A dog standing at a door entrance with a wooden floor and a mat with paw prints.
A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

6. the Alander

the Alander
Copake
United States
Luis
₩186,347
₩208,709 total
includes taxes & fees
Oct 31 - Nov 1
the Alander
A modern hotel lobby with seating areas, tables, and a reception desk.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A kitchenette with a microwave, coffee maker, and coffee cups.
A breakfast area with a counter, coffee machine, and a display of pastries.

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
United States
Cynthia
₩110,743
₩123,700 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.
A motel with a parking lot and several cars parked.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

8. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
United States
Andrea
₩79,663
₩88,980 total
includes taxes & fees
Nov 19 - Nov 20
Monument Mountain Motel
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.
A motel with a two-story structure, multiple rooms with red doors, and a central staircase.
A living room with a patterned carpet, two sofas, a dining table, and chairs.
A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

9. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
United States
Ramakrishnan
₩105,153
₩117,456 total
includes taxes & fees
Oct 31 - Nov 1
Travelodge by Wyndham Great Barrington Berkshires
A large house with a balcony and a grassy yard.
A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

10. The Little Lion

The Little Lion
Great Barrington
United States
Lidia
₩137,764
₩153,882 total
includes taxes & fees
Nov 19 - Nov 20
The Little Lion
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

11. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
₩209,667
₩300,324 total
includes taxes & fees
Nov 15 - Nov 16
The Red Lion Inn
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A grassy outdoor area with four blue Adirondack chairs arranged in a circle.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

12. East Rock Inn

East Rock Inn
Great Barrington
United States
Sharon
₩177,162
₩197,890 total
includes taxes & fees
Nov 4 - Nov 5
East Rock Inn
A dining table with pastries, a coffee pot, and a vase of sunflowers.
A bedroom with a wooden bed, bedside tables, a desk, and a chair.
A large, two-story white building with a symmetrical facade, columns, and a central entrance.
A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

13. Granville House

Granville House
Housatonic
United States
Cynthia
₩338,900
₩378,554 total
includes taxes & fees
Oct 25 - Oct 26
Granville House
Interior detail
A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.
A bedroom with a large bed, a dresser, a chair, and a mirror.
A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

14. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Mark
₩218,110
₩243,629 total
includes taxes & fees
Oct 28 - Oct 29
Wilder House Berkshires
A balcony with a table featuring a bottle, glasses, and binoculars, overlooking a river, greenery, and a house.
A bar with a patterned floor, bar stools, and a bar counter with taps.
A dining area with a brick fireplace, wooden beams, and a chandelier.
A reception area with a wooden desk, a blue wall with a logo, and shelves with products.

15. Diamond Mills Resort

Diamond Mills Resort
Saugerties
United States
luping
₩354,617
₩430,522 total
includes taxes & fees
Oct 21 - Oct 22
Diamond Mills Resort
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

16. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
₩141,431
₩157,977 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

17. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Lucinda
₩123,618
₩138,081 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Lee - Lenox South
A two-story house with a brick entrance and a white facade.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A neatly arranged bedroom with a bed, bedside table, and a dresser.

18. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
United States
Philippe
₩509,581
₩616,449 total
includes taxes & fees
Nov 4 - Nov 5
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside dock with kayaks and a covered boat ramp.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lodge with a large building and a dock by a lake, surrounded by forest.

19. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
₩149,344
₩166,818 total
includes taxes & fees
Nov 15 - Nov 16
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

20. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
₩173,705
₩194,028 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
View all properties

Hotels recommended for families in Hillsdale

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.
A snow-covered landscape with a house and a sign that reads "the brooks".
A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.
A compact kitchen with a wooden countertop, a coffee machine, and a small shelf with a hair dryer and cups.

The Brooks Motel

The Brooks Motel
Hillsdale
₩194,534
₩217,880 total
includes taxes & fees
Oct 21 - Oct 22
The Brooks Motel
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

The Yankee Inn

The Yankee Inn
Lenox
₩141,431
₩157,977 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.
A motel with a parking lot and several cars parked.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

Monument Mountain Motel

Monument Mountain Motel
Great Barrington
₩79,855
₩89,195 total
includes taxes & fees
Nov 1 - Nov 2
Monument Mountain Motel
A modern hotel lobby with seating areas, tables, and a reception desk.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A kitchenette with a microwave, coffee maker, and coffee cups.
A breakfast area with a counter, coffee machine, and a display of pastries.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
₩110,743
₩123,700 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
₩191,665
₩214,090 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A grassy outdoor area with four blue Adirondack chairs arranged in a circle.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

East Rock Inn

East Rock Inn
Great Barrington
₩177,162
₩197,890 total
includes taxes & fees
Nov 4 - Nov 5
East Rock Inn
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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

6.4/10 (5 reviews)
Scale New England's largest aerial adventure park with over 150 treetop challenges across nine difficulty levels. Glide between zip lines and navigate bridges while surrounded by serene forest scenery.
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Copake Lake

This glacial lake in the Hudson Valley offers pristine waters for boating, fishing, and swimming year-round. Enjoy serene morning kayaking or lively afternoons of water skiing surrounded by picturesque natural scenery.
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Hillsdale Town Hall

This historic former library now serves as Hillsdale's administrative center with distinctive slate-shingled roof and Ionic columns. Visit during town board meetings to experience local governance.
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Community Library

The Roeliff Jansen Community Library serves as a vital cultural hub for Hillsdale, Copake, and Ancram communities. Visitors enjoy book clubs, writing groups, and educational workshops in its welcoming atmosphere.
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Mosquito Island

Commune with nature and explore the great outdoors at Mosquito Island during your travels in Copake Lake.
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Roe Jan Brewing Co.

After visiting Roe Jan Brewing Co., make a plan to see the other sights and activities in Hillsdale. Discover the sunrises while you're in the area.
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Learn more about Hillsdale

Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.

See all hotels in Hillsdale
A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.

Top Hillsdale Hotel Reviews

St. Charles Hotel

St. Charles Hotel

8/10 Good
"I stayed at this hotel for an event. There were people in my party who did not have a great experience, but I was given a nice sized room and easy check in and did not have a single problem. The staff was really nice though not always at the desk."
Chike 2-night trip
Posted less than an hour ago
St. Charles Hotel
Hotel On North

Hotel On North

10/10 Excellent
"Well maintained and updated property. Very kind and helpful team."
Michele 1-night trip
Posted 1 hour ago
Hotel On North
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
Mallory 1-night trip
Posted 2 hours ago
The Red Lion Inn
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"Traveling with my husband for NY Sheep and Wool Festival. Worked for what we needed. Could use updating."
Cheri 2-night trip
Posted 5 hours ago
Howard Johnson by Wyndham Saugerties
Berkshires Untold

Berkshires Untold

8/10 Good
"We were surprised when we arrived to find that the hotel was actually a converted motel. The website doesn’t show any pictures to indicate this which is a bit of false advertising. But we were able to look past that because the lobby/restaurant area was very cute and cozy. Nice breakfast options and free coffee and tea (but they only offered 1 variety of tea). Rooms were pretty standard, bathroom was bigger than I anticipated. Loved the Le Labo products- nice touch. Rooms were clean, but we realized that housekeeping never came the 3 nights we were there. Not sure if we were supposed to request it each day, but it was kinda strange that they never even came to clear out the garbage cans. The outdoor patio was nice but it was a bit too cold for us to use even though they did have fire pits. Not sure I would go back. If was also on a main road so you could hear the cars & trucks. I’d probably look for better options in the area before I settled on this again."
Natalie 3-night trip
Posted 6 hours ago
Berkshires Untold
Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Large , clean suite .well equipped kitchen. Comfortable stay! Would definitely return."
ulla 1-night trip
Posted 6 hours ago
Berkshire Mountain Lodge
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"10/10 experience! Can’t wait to go back! One overnight stay isn’t enough stay for multiple days!!!!"
Briana 1-night trip
Posted 7 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Great place to stay, super friendly staff. All that the Lenox and Lee had to offer isn't far. Will stay again."
Jason 1-night trip
Posted 11 hours ago
The Cornell Inn, Lenox & The Berkshires
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"G"
Ryan 1-night trip
Posted 1 day ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

More cheap stays in Hillsdale

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
₩94,638
₩105,710 total
Oct 21 - Oct 22
includes taxes & fees
5.4/10 (925 reviews)
FairBridge Inn Express
Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
₩100,694
₩112,475 total
Nov 9 - Nov 10
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Quality Inn Great Barrington
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA
₩126,754
₩141,584 total
Nov 17 - Nov 18
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
₩141,431
₩157,977 total
Nov 1 - Nov 2
includes taxes & fees
The Yankee Inn
St. Charles Hotel

St. Charles Hotel

16 Park Place Hudson NY
₩169,709
₩191,778 total
Nov 20 - Nov 21
includes taxes & fees
6.6/10 (1,004 reviews)
St. Charles Hotel
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

549 Washington Street Hudson NY
₩312,214
₩413,111 total
Nov 15 - Nov 16
includes taxes & fees
8.6/10 Excellent! (92 reviews)
Pocketbook Hotel and Bath

Frequently asked questions

Where is the best place to stay in Hillsdale?
Located 20.9 mi (33.7 km) from the heart of Hillsdale, Berkshire Mountain Lodge is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Quality Inn Great Barrington and Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy. See all available top hotels, or vacation rentals in Hillsdale.
If I need to cancel my hotel reservation in Hillsdale, will I receive a refund?
Yes! You'll find that most room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.
Where can I learn more about changing or cancelling my trip to Hillsdale?
To access more information about changing or cancelling your trip to Hillsdale, head over to our customer service page.
What's the best pet-friendly accommodation in Hillsdale?
The Brooks Motel is a top pet-friendly option for your stay. See more pet-friendly hotel accommodations in Hillsdale.
Where is the best hotel to stay close to Catamount Aerial Adventure Park?
Catamount Lodging is one of the top choices for your stay based on our traveler data, and this aparthotel offers private balconies and free WiFi. It's located just a short 0.3 mi (0.5 km) from Catamount Aerial Adventure Park. Another good option is Holiday House Motel, located 1.2 mi (2 km) away.
What are some accommodations with pools in Hillsdale?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Pocketbook Hotel and Bath and The Yankee Inn are a couple of other choices with an onsite pool. View all hotels with pools in Hillsdale.
What is the best hotel near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What's it like staying in Hillsdale?
Visitors can enjoy all that Hillsdale has to offer including the coffeehouses and ski areas. This city also attracts tourists with its relaxing and quaint setting. In Hillsdale, there are 59 hotels and other accommodations to choose from. Find out more about Hillsdale.
What should I do while I'm visiting Hillsdale?
The picturesque setting of Copake Lake and Mosquito Island exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Catamount Aerial Adventure Park and Catamount Ski Area. Check out what more to see and do in Expedia's Hillsdale guide.
What's the weather like in Hillsdale?
The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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